Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers

Alexander S Henderson, Sandra Medina, John F Bower, M Carmen Galan

Research output: Contribution to journalArticle (Academic Journal)peer-review

52 Citations (Scopus)

Abstract

A general and practical route to carbohydrate-aryl ethers by nucleophilic aromatic substitution (SNAr) is reported. Upon treatment with KHMDS, C-O bond formation occurs between carbohydrate alcohols and a diverse range of fluorinated (hetero)aromatics to provide the targets in good to excellent yields. Commercially available arylating agents, high atom economy, and high regioselectivity are notable features of the protocol. The aryl ether products have potential for wide-ranging applications as exemplified by the synthesis of a novel chiral P,N-ligand.

Original languageEnglish
Pages (from-to)4846-4849
Number of pages4
JournalOrganic Letters
Volume17
Issue number19
Early online date17 Sept 2015
DOIs
Publication statusPublished - 2 Oct 2015

Structured keywords

  • BCS and TECS CDTs

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